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LIBRARY 

STATE PLAMp BOARD E-840 



United States Department of Agriculture 

Agricultural Research Administration 

Bureau of Entomology and Plant Quarantine 



LABORATORY TESTS OF TOXICITY OF SOME ORGANIC COMPOUNDS 
TO THE EUROPEAN CORN BORER, 1947 to 1952 

By D. D. Questel, Division of Cereal and Forage Insect Investigations, 
and S. I. Gertler, Division of Insecticide Investigations 



The results of laboratory tests with some organic compounds against 
newly hatched larvae of the European corn borer ( Pyrausta nubilalis 
(Hbn.)) at Toledo, Ohio, and Ankeny, Iowa, are herein reported. These 
tests were conducted by the Division of Cereal and Forage Insect Investi- 
gations from 1947 through 1950. Similar tests with other compounds 
have been reported in E-557, E-612, E-620, E-707, E-748, E-778, and 
E-781 of this Bureau. All were supplied by the Division of Insecticide 
Investigations. 

The care and handling of moths, eggs, and larvae and the technique 
employed in conducting these tests are described in E-557. In the initial 
tests either 2 or 4 pounds of the compound was used per 100 gallons of 
water containing 1/3 pound of a sodium monosulfonate of butylphenylphenol 
as a wetting agent. All compounds had been ground with an equal weight 
of clay. Most of them were sprayed at the 4-pound concentration on 
fresh green corn leaves. The few compounds first tested at 2 pounds 
were sprayed on fresh cauliflower leaves. For each test approximately 
the same number of larvae were used in the treated and untreated checks. 
All larvae were given an opportunity to feed for 48 hours before mortality 
readings were taken. Materials showing a mortality of 10 percent or 
higher in the initial tests were retested at lower concentrations. Results 
of these tests are given in table 1. Results with materials showing less 
than 10 percent mortality are given in table 2. The mortality in the 
checks was never higher than 2 percent. 



2- 



Table 1. --Results against the European corn borer of toxicity tests with organic 
compounds that showed a mortality of 10 percent or more in initial tests and 
were retested at lower concentrations given in order of effectiveness 



Compound 



Concen- 
tration per 
100 gallons 



Borers 
used 



Feeding 



Average 
mortality 



Benzoic acid, cinnamylidene- 

hydrazide 
Cg H 5 CONHN:CHCH:CHC 6 H 5 



Methane, tetrakis- 
( chlorom ethyl) - 
C(CH 2 C1) 4 



Ether, 2,4-dinitrophenyl phenyl 
C 6 H 3 (N0 2 ) 2 OC 6 H 5 



Ether, 2,4-dinitrophenyl phenethyl 
C6H3(N02)20CH 2 CH 2 C6H5 



Benzoic acid, o-(2,4- 

dinitrophenoxy) - 
(N0 2 ) 2 C 6 H 3 OC 6 H 4 COOH 



Benzoic acid, p-nitro- 

cinnamylidenehydrazide 
N0 2 C 6 H 4 CONHN:CHCH:CHC 6 H 5 

Ether, 2-cyclohexyl-4,6- 

dinitrophenyl 2,4-dinitrophenyl 
C6H3(N0 2 ) 2 OC6H2(C6Hi l)(N0 2 )2 

2-Cyclohexene-l-one, 

2,3,4, 4,5,6,6-heptachloro 
CCl:CClCCl 2 CHClCCl 2 CO 



Pounds 


Number 


Percent 


4 


65 


None 


100 


2 


65 


None to little 


99 


1 


146 


do. 


67 


1/2 


71 s 


Moderate 


24 


1/4 


62 


do. 


11 


4 


125 


None 


100 


2 


289 


do. 


83 


1 


305 


Much 


12 


1/2 


332 


do. 


2 


4 


87 


None 


100 


2 


92 


Moderate 


62 


1 


46 


do. 


42 


4 


45 


None 


100 


2 


42 


Moderate 


46 


1 


24 


Much 





4 


121 


None to little 


98 


2 


75 


Moderate 


69 


1 


94 


Much 


25 


1/2 


89 


do. 


4 


4 


85 


None 


99 


2 


117 


None to much 


37 


1 


71 


Moderate to much 


18 


4 


106 


None 


95 


2 


54 


Moderate 


85 


1 


48 


Much 


69 


4 


174 


Little 


95 


2 


99 


Moderate 


8 


1 


77 


Much 


3 



-3- 



Table 1. --(Continued) 



Compound 



Concen- 
tration per 
100 gallons 



Borers 
used 



Feeding 



Average 
mortality 



Ether, 2,4-dinitrophenyl 

4-methylcyclohexyl 
C 6 H 3 (NO 2 )2OC 6 H 10 CH3 



Ether, benzyl 2,4-dinitrophenyl 
C 6 H 3 (N0 2 ) 2 OCH 2 C 6 H 5 



Ethane, l-(jD-tert-butylphenoxy)- 

2 -( 2, 4-dinitrophenoxy) - 
(N0 2 ) 2 C 6 H 3 OC 2 H40C 6 H 4 C(CH3)3 

Ether, cyclohexyl 2,4-dinitrophenyl 4 
C 6 H 3 (N0 2 ) 2 OC 6 H 11 

Benzoic acid, piper onylidene- 

hydrazide 
C 6 H 5 CONHN:CHC 6 H 3 :0 2 CH 2 

Ether, 2,4-dinitrophenyl 

tetrahydrofurfuryl 
C 6 H 3 (N0 2 ) 2 OCH 2 CH(CH 2 ) 3 



L 



Phenetole, 2,4-dinitro- 
C 6 H 3 (N0 2 ) 2 OC 2 H 5 

Benzoic acid, alpha-methyl- 

benzylidenehydrazide 
C 6 H 5 CONHN:C(CH 3 )C6H 5 

p - Toluhydr oquinone 
CH 3 C 6 H 3 (OH) 2 



Pounds 


Numb 


er 


Percent 


4 


108 


None 


92 


2 


107 


Moderate 


78 


1 


88 


Much 


45 


1/2 


83 


do. 


10 


4 


37 


None to little 


84 


2 


47 


Little to moderate 


64 


1 


26 


Much 


19 


4 


96 


Much 


83 


2 


66 


do. 


33 


1 


80 


do. 


13 


A 4 


37 


Little 


81 


2 


28 


Much 





4 


65 


None to little 


77 


2 


84 


Much 


52 


1 


59 


Much 


3 


4 


33 


None to moderate 


70 


2 


40 


Moderate to much 


41 


1 


29 


Much 


21 


4 


34 


Moderate 


62 


2 


21 


Much 


10 


1 


22 


do. 


9 


4 


69 


None to much 


50 


2 


135 


Much 


1 


4 


75 


Moderate 


37 


2 


97 


Much 


8 



-4- 



Table 1. --(Continued) 



Compound 



Concen- 
tration per 
100 gallons 



Borers 
used 



Feeding 



Average 
mortality 



p-Quinone, 2,5-di-tert-butyl- 
0:C 6 H2/C"(CH 3 g7 2 :0 

Acetaldehyde, 2-chloroethyl 

2,4,5- trichlorophenyl acetal 
CH 3 CH(OCH2CH 2 Cl)OC 6 H2Cl3 

Ether, p-(alpha, alpha-dimethyl- 

benzyl)phenyl 2,4-dinitrophenyl 
C 6 H3(N0 2 ) 2 OC 6 H 4 C(CH3) 2 C 6 H 5 

Ether, p-tert-butylphenyl 

2, 4-dinitrophenyl 
C 6 H 3 (N0 2 ) 2 OC 6 H 4 C(CH 3 )3 

Aniline, N-allyl-2,4-dinitro- 
(N0 2 ) 2 C 6 H 3 NHCH 2 CH:CH 2 



Pounds 


Numb 


er 


Pe 


rcent 


4 


112 


Moderate 




30 


2 


100 


Much 




2 


4 


49 


Moderate to much 




29 


2 


64 


Much 







4 


49 


. 




18 


2 


39 


- 




8 


1 


35 


- 







4 


45 


_ 




13 


2 


31 


- 




9 


1 


24 


- 







4 


134 


_ 




10 


2 


91 


- 




1 



-5- 



Table 2. --Results against the European corn borer of toxicity tests with organic 
compounds showing less than iU percent mortality in order of effectiveness 



Compound 



Concen- 
tration per 
100 gallons 



Borers 
used 



Average 
mortality 



Pounds Number Percent 



O-Ethyl 0,0-bis(p-nitrophenyl) thiophosphate 4 135 

C 2 H 5 OP(S)(OC 6 H 4 N0 2 )2 

Acetic acid, 4,6-dinitro-o-toloxy- 2 173 

(N0 2 ) 2 (CH 3 ) C 6 H 2 OCH 2 COOH 

Benzoic acid, p-nitro-,alpha-methylbenzylidene- 4 178 

hydrazide 
N0 2 C 6 H 4 CONHN:C(CH 3 )C 6 H 5 

Benzaldehyde, 3-methoxy-4-(2,4-dinitrophenoxy)- 4 105 

C 6 H3(N0 2 ) 2 OC 6 H 3 (OCH 3 )CHO 

Phenol, 2-chloro-4,6-dinitro- 2 218 

C1C 6 H 2 (N0 2 ) 2 (0H) 

Aniline, 2,5-dimethoxy- 4 115 

NH 2 C 6 H 3 (OCH 3 ) 2 

Benzene, l,3-bis(2,4-dinitrophenoxy)- 4 113 

C 6 H 4^C 6 H 3 (N0 2 j^ 2 

Benzene, l,4-bis(2,4-dinitrophenoxy)- 4 93 

C 6 H 4 ^C 6 H 3 (N0 2 ) 2 7 2 

Benzoic acid, £-nitro-,£-chlorobenzylidene- 4 74 

hydrazide 

N0 2 C6H4C0NHN:CHC6H4C1 

Benzoic acid, _p-nitro-2, 2, 2-trichloroethylidene- 4 101 

hydrazide 
N0 2 C 6 H 4 C0NHN:CHCC1 3 



-6- 



Table 2. --(Continued) 



Compound 



Concen- 
tration per 
100 gallons 



Borers 
used 



Average 
mortality 



Pounds Number Percent 



Ethanol, 2,2'-(phenylimino)di- 4 

C 6 H 5 N(C 2 H 4 OH) 2 

Ether, p-chlorophenyl 2,4-dinitrophenyl 4 

C 6 H 3 (N0 2 ) 2 OC 6 H 4 Cl 

Ether, o-cyclohexylphenyl 2,4-dinitrophenyl 4 

C 6 H 3 (N0 2 ) 2 OC 6 H 4 C 6 H 11 

Ether, 2,4-dinitrophenyl o-nitrophenyl 4 

C 6 H 3 (N0 2 ) 2 OC 6 H 4 N0 2 

Ether, 2,4-dinitrophenyl j>-tolyl 4 

C 6 H 3 (N0 2 ) 2 OC 6 H 4 CH 3 

Ether, 2,4-dinitrophenyl 2,4,6 -trichlorophenyl 4 

C 6 H 3 (N0 2 ) 2 OC 6 H 2 Cl 3 

Acetic acid, 2,4-dinitrophenoxy- 2 

(N02)2C6H30CH2COOH 

Aniline, 2,5-diethoxy- 4 

NH 2 C 6 H 3 (OC 2 H 5 ) 2 

Ether, 2,4-dichlorophenyl 2,4-dinitrophenyl 4 

C 6 H 3 (N0 2 ) 2 OC 6 H 3 Cl 2 

Ether, 2,4-dinitrophenyl 2-nitro-£-tolyl 4 

C 6 H 3 (N0 2 ) 2 OC 6 H 3 (N0 2 )CH 3 

Phenol, p-methoxy- 4 

HOC 6 H 4 OCH 3 



117 



102 



43 



84 



73 



81 



231 



124 



71 



98 



103 



- 7 



Table 2. --(Continued) 



Compound 



Concen- 
tration per 
100 gallons 



Borers 
used 



Average 
mortality 



Acetic acid, o-cyclohexylphenoxy- 
(C6Hn)C6H40CH2COOH 



Pounds 



Number Percent 



186 



Anisole, 5-allyl-2-(2,4-dinitrophenoxy) 
(N0 2 ) 2 C 6 H 3 OC 6 H3(OCH3)CH 2 CH:CH 2 



117 



Benzoic acid, p-nitrocyclopentylidenehydrazide 4 
N0 2 C 6 H 4 CONHN:C(CH 2 ) 2 CH 2 

Benzoic acid, p-nitro-,2-ethylbutylidenehydrazide 4 
N0 2 C 6 H 4 CONHN:CHCH(C 2 H 5 )CH 2 CH 3 



183 



73 



Benzoic acid, p-nitromethylenehydrazide 
N02C6H4CONHN:CH 2 



247 



Ethanol, 2,2'-(m-tolylimino)di- 
CH 3 C 6 H 4 N(C 2 H 4 OH) 2 



103 



Ether, £-chlorophenyl 2,4-dinitrophenyl 
C 6 H3(N02)20C6H4C1 



78 



Ether, 2,4-dinitrophenyl 2-naphthyl 
C 6 H 3 (NO 2 ) 2 OC 10 H 7 



78 



p-Nitrophenyl phosphate 
rC 6 H 4 N0 2 ) 3 P0 4 



229 



Phenol, o-benzylideneamino- 
C 6 H 5 CH:NC 6 H 4 OH 



106 



p-Quinone, 2,3,5-trichloro-6-phenyl 
0:C 6 (C 6 H 5 )C1 3 :0 



121 



- o 



Table 2. --(Continued) 



Compound 



Concen- 
tration per 
100 gallons 



Borers j Average 
used (mortality 



- : uenesulfonic acid, o- I aexyl-4 B 
dmitropheny] ester 

CH3C 5 H 4 S0 3 C 5 H 2l N0 2 ) 2 .C 3 H i: ) 



Pounds 



Number Percent 



223 



m-Toluic acid 2-(2,2-dini:rophenoxy 
CH3C6H3(COOH)OC6H3(N02)2 



:4i 



esulfonic acid., 2,4-dinitrophenyl ester 2 
CH3C 5 H 4 S0 3 C 6 H3iX0 2 ) 2 



233 



Aniline, N-sec-butyl-2, 4 -dir.it 
(N0 2 ) 2 C 6 H 3 NHCH(C2H 5 )CH 3 



209 



Benzoic acid, isopropylidenehydrazide 
C 6 H-CONHX:C(CH 3 ) 2 * 



72 



Benzoic acid, p-nitro-j cyclohexylidenehydrazide 4 
N0 2 C 5 H 4 CONHX:C(CH 2 )* 4 CH 2 

Ether j 2-b:phenylvl 2,4-dinitropbeny] 4 

C 6 H 5 C 6 H 4 OC 6 H 3 (N0 2 ) 2 



167 



127 



Hvdroquinone, 2,5-di-tert-bu:yl- 
C5H 2 (OH) 2 C"(CH 3 )J 2 



87 



Phenol, p-butylamino- 

HOC ^H^InHC 4.H i 



147 



Phenol, c- - nlorobenzylideneamino)- 
ClC-H.CHrNCeH-OH 



127 



p- Toluene sulfonic acid, 4,6-dinitro-o-tolyl ester 2 
CH 3 C 5 H 4 S0 3 C 5 H 2 (CH3)(N-0 2 ) 2 



209 



Table 2. —(Continued) 



C: 



Ccr.ier. 

alien : 



- 
usee rr.:r:a.::; 



Ether . 4-:er:-bu:yl-2- ihlcr: phenyl 

2.4-d:n::r;in envl 
C 6 H 3 (N0 2 ) 2 0C 6 H 3 C1C(CH 2 



P 



_ 



? E . 



I .r 



Phenol. 4-chloro-2,6-dinitro- 
C:C 6 H 2 (N0 2 ) 2 (OH) 



L95 



Benzc:: s.c:d ; p-rh/:ro-. alpha-: 

hydrazine 
H0 2 C 6 H 4 COXHX:C(CH3)C 2 H 5 



1-- 



.\ 



Ether, 2,4-dinitrophenyl 1-r.ap 
C 6 H 3 (N0 2 ; 2 OC- i: H T 



74 



.: 



Ether, 2,4-dinitrophenyl p-tolyl 
C 6 H 3 (N0 2 )20C 6 H 4 CH3 



": 



.: 



Phenol, o-(o-chlorobenzylideneamino)- 



ClC 6 H 4 CH:NC 6 H 4 OB 



4 



;-.-. 



.8 



Benzvlamine.. N-(2. 4-dinitropheny] 

C 6 H 5 CH 2 NHC 6 H 3 (X0 2 ) 2 



127 



." 



Glycine, N-( 2, 4 -dirhtr : prenyl) 
(Nb 2 ) 2 C 3 H 3 NHCH 2 CCMDH 



154 



1.. 5-Naphthalenedic '. 
C 10 H 6 (OH) 2 



: : : 



Phenrl, :- ar:syl:derearr.:r.: - 
CH.OC JLCHiNCcH -OH 

i D 9 ~ 

Phenol . p-(2,4-dinitro ?.nilino) • 

(xo 2)2 c7h 3 xhc 6 h 4 oh 









- 10 - 



Table 2. --(Continued) 



Compound 



Concen- 
tration per 
100 gallons 



Borers 
used 



Average 
mortality 



Pounds 



Number Percent 



Benzoic acid, p-nitrobutylidenehydrazide 
N0 2 C 6 H 4 CONHN:CHCH 2 CH 2 CH 3 



192 



0.6 



Ethanol, 2-(2,4-dinitrophenoxy)- 
(N02)2C6H30C2H40H 

Ether, 2, 4-dinitrophenyl m-nitrophenyl 
C 6 H 3 (N0 2 )20C 6 H 4 N02 



125 



90 



.6 



.6 



Naphthalene, 1 , 5 -bis( 2, 4-dinitrophenoxy) - 
/fNO2)2C6H3O/2Cl0H6 

Phenol, o-(2,4-dinitroanilino)- 
OHC6H4NHC6H 3 (N02)2 

Acetanilide, alpha, alpha, alpha, 4-tetrachloro- 
CCI3CONHC6H4CI 

Benzoic acid, p-nitroisopropylidenehydrazide 
N0 2 C 6 H 4 CONHN:C(CH 3 ) 2 

Dibenzylamine, N-( 2, 4-dinitrophenyl) - 
(N0 2 )2C 6 H3N(CH 2 C 6 H 5 )2 

Benzoic acid, p-nitro-, hydrazide 
NO2C6H4CONHNH2 

Benzoic acid, p-nitro-piperonylidenehydrazide 
N0 2 C 6 H 4 CONHN:CHC 6 H 3 :0 2 CH 2 

Sulfide, bis(2, 4-dinitrophenyl) 
^ 6 H 3 (N0 2 )^ 2 S 



155 



147 



138 



193 



174 



244 



189 



248 



.6 



.6 



.5 



.5 



.5 



.4 



.4 



.4 



11 - 



Table 2. --(Continued) 



Compound 



Concen- 
tration per 
100 gallons 



Borers 
used 



Average 
mortality 



Pounds Number Percent 



Acetsnilide, alpha, alpha, 4-trichloro 
CHCl 2 CONHC 6 H 4 Cl 



150 



m-Acetotoluidide, alpha, alpha, alpha-trichloro- 

alpha^, alpha"*, alpha^-trifluoro- 
CCl 3 CONHC 6 H 4 CF 3 



136 



Aniline, N-sec-butyl-2,4-dinitro- 
(N0 2 ) 2 C 6 H 3 NHCH(C 2 H 5 )CH 3 



134 



Benzamide, N-(2-hydroxyethyl)-p-nitro- 
NO2C6H4CONHCH2CH2OH 



143 



Benzoic acid, p-nitrobenzylidenehydrazide 
N02C6H4CONHN:CHC6H5 



213 



Benzoic acid, p-nitro-propylidenehydrazide 
N0 2 C 6 H 4 CONHN:CHCH 2 CH 3 



180 



o-Cresol, alpha-(o-hydroxyphenylimino) 
OHC 6 H 4 CH:NC 6 H 4 OH 



147 



Cyclohexylamine, N-(2,4-dinitrophenyl) 
C 6 H n NHC 6 H 3 (N0 2 ) 2 



118 



Ethanol, 2-(2 J 4-dinitroanilino) 
(N0 2 ) 2 C 6 H 3 NHCH 2 CH 2 OH 



122 



Ether, 4-biphenylyl 2,4-dinitrophenyl 
C 6 H 5 C 6 H 4 OC 6 H 3 (N0 2 ) 2 



130 



Ether, 2-bromo-4-tert-butylphenyl 

2, 4-dinitrophenyl 
(N0 2 ) 2 C 6 H 3 OC 6 H 3 (Br)C(CH 3 ) 3 



100 



UNIVERSITY OF FLORIDA 



-12- 



3 1262 09239 6422 



Table 2. --(Continued) 



Compound 



Concen- 
tration per 
100 gallons 



Borers 
used 



Average 
mortality 



Pounds Number Percent 



Ether, p-bromophenyl 2,4-dinitrophenyl 
C 6 H 3 (N0 2 ) 2 OC 6 H4Br 



92 



Ether, 2,4-dinitrophenyl p-nitrophenyl 
C 6 H 3 (N0 2 )20C 6 H 4 N0 2 



52